# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       wwang@unm.edu
_publ_contact_author_name        'Wei Wang'
loop_
_publ_author_name
'Jing Deng'
'Fei Wang'
'Wenzhong Yan'
'Jin Zhu'
'Hualiang Jiang'
'Wei Wang'
'Jian Li'

data_mo_dm11173_0m
_database_code_depnum_ccdc_archive 'CCDC 844031'
#TrackingRef 'mo_dm11173_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Cl N O5 S'
_chemical_formula_weight         381.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.0413(8)
_cell_length_b                   13.8240(12)
_cell_length_c                   13.9065(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1738.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      30.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8821
_exptl_absorpt_correction_T_max  0.9041
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12518
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3790
_reflns_number_gt                3732
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.3551P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3790
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.06969(4) 0.69566(3) 0.33416(3) 0.03691(10) Uani 1 1 d . . .
S1 S 0.46404(3) 0.98976(2) 0.19390(2) 0.01782(7) Uani 1 1 d . . .
N1 N 0.53854(12) 0.83399(7) 0.28985(7) 0.0207(2) Uani 1 1 d . . .
O1 O 0.08824(11) 0.84328(9) -0.08526(7) 0.0336(2) Uani 1 1 d . . .
O2 O 0.52012(11) 1.04500(7) -0.02849(7) 0.0288(2) Uani 1 1 d . . .
O3 O 0.70549(10) 0.94422(7) 0.01156(7) 0.0249(2) Uani 1 1 d . . .
O4 O 0.60831(10) 1.03213(7) 0.20678(7) 0.0264(2) Uani 1 1 d . . .
O5 O 0.33629(10) 1.05176(6) 0.18915(7) 0.02397(19) Uani 1 1 d . . .
C1 C 0.20779(15) 0.81055(10) -0.10450(9) 0.0252(3) Uani 1 1 d . . .
H1 H 0.2152 0.7689 -0.1586 0.030 Uiso 1 1 calc R . .
C2 C 0.34594(14) 0.83116(10) -0.04858(9) 0.0218(3) Uani 1 1 d . . .
H2A H 0.4171 0.8649 -0.0911 0.026 Uiso 1 1 calc R . .
H2B H 0.3913 0.7690 -0.0292 0.026 Uiso 1 1 calc R . .
C3 C 0.32098(13) 0.89324(9) 0.04209(9) 0.0168(2) Uani 1 1 d . . .
H3 H 0.2727 0.9552 0.0223 0.020 Uiso 1 1 calc R . .
C4 C 0.47366(13) 0.91698(8) 0.08511(8) 0.0165(2) Uani 1 1 d . . .
H4 H 0.5267 0.8552 0.0997 0.020 Uiso 1 1 calc R . .
C5 C 0.56745(13) 0.97723(9) 0.01570(9) 0.0191(2) Uani 1 1 d . . .
C6 C 0.80549(17) 1.00073(12) -0.04826(12) 0.0354(3) Uani 1 1 d . . .
H6A H 0.7648 1.0058 -0.1134 0.053 Uiso 1 1 calc R . .
H6B H 0.9022 0.9688 -0.0508 0.053 Uiso 1 1 calc R . .
H6C H 0.8167 1.0656 -0.0209 0.053 Uiso 1 1 calc R . .
C7 C 0.22086(13) 0.84269(9) 0.11467(8) 0.0165(2) Uani 1 1 d . . .
C8 C 0.09214(14) 0.88761(9) 0.14670(9) 0.0198(2) Uani 1 1 d . . .
H8 H 0.0658 0.9493 0.1219 0.024 Uiso 1 1 calc R . .
C9 C 0.00135(14) 0.84312(10) 0.21473(9) 0.0225(3) Uani 1 1 d . . .
H9 H -0.0864 0.8739 0.2365 0.027 Uiso 1 1 calc R . .
C10 C 0.04186(14) 0.75323(10) 0.24979(9) 0.0219(2) Uani 1 1 d . . .
C11 C 0.16888(14) 0.70675(9) 0.21934(9) 0.0212(3) Uani 1 1 d . . .
H11 H 0.1948 0.6451 0.2445 0.025 Uiso 1 1 calc R . .
C12 C 0.25822(13) 0.75190(9) 0.15118(9) 0.0191(2) Uani 1 1 d . . .
H12 H 0.3455 0.7206 0.1293 0.023 Uiso 1 1 calc R . .
C13 C 0.43467(14) 0.90287(8) 0.28685(8) 0.0176(2) Uani 1 1 d . . .
C14 C 0.31480(15) 0.91135(9) 0.34776(9) 0.0208(2) Uani 1 1 d . . .
H14 H 0.2455 0.9626 0.3416 0.025 Uiso 1 1 calc R . .
C15 C 0.30081(16) 0.84063(10) 0.41892(9) 0.0259(3) Uani 1 1 d . . .
H15 H 0.2213 0.8428 0.4635 0.031 Uiso 1 1 calc R . .
C16 C 0.40461(17) 0.76747(10) 0.42336(10) 0.0269(3) Uani 1 1 d . . .
H16 H 0.3965 0.7181 0.4706 0.032 Uiso 1 1 calc R . .
C17 C 0.52135(16) 0.76656(9) 0.35800(10) 0.0248(3) Uani 1 1 d . . .
H17 H 0.5919 0.7158 0.3620 0.030 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.03128(18) 0.0463(2) 0.03311(18) 0.00983(15) 0.01102(14) -0.00972(15)
S1 0.01925(14) 0.01485(13) 0.01935(13) -0.00066(10) -0.00096(11) -0.00197(10)
N1 0.0210(5) 0.0197(5) 0.0214(5) -0.0020(4) -0.0028(4) 0.0020(4)
O1 0.0211(5) 0.0509(6) 0.0289(5) -0.0050(5) -0.0039(4) -0.0035(5)
O2 0.0243(5) 0.0294(5) 0.0328(5) 0.0112(4) 0.0003(4) -0.0023(4)
O3 0.0165(4) 0.0285(5) 0.0297(5) 0.0025(4) 0.0058(4) -0.0010(4)
O4 0.0253(5) 0.0268(5) 0.0271(5) -0.0025(4) -0.0022(4) -0.0104(4)
O5 0.0273(5) 0.0165(4) 0.0281(5) 0.0004(4) 0.0004(4) 0.0030(3)
C1 0.0236(6) 0.0318(7) 0.0202(6) -0.0026(5) 0.0010(5) -0.0083(5)
C2 0.0173(6) 0.0287(6) 0.0193(6) -0.0043(5) 0.0017(5) -0.0037(5)
C3 0.0131(5) 0.0193(5) 0.0180(5) 0.0004(4) -0.0001(4) -0.0008(4)
C4 0.0143(5) 0.0175(5) 0.0179(5) -0.0004(4) 0.0001(5) -0.0006(4)
C5 0.0165(5) 0.0210(5) 0.0197(5) -0.0014(4) 0.0003(4) -0.0035(4)
C6 0.0241(7) 0.0399(8) 0.0423(8) 0.0034(7) 0.0144(6) -0.0057(7)
C7 0.0146(5) 0.0188(5) 0.0162(5) -0.0016(4) -0.0005(4) -0.0030(4)
C8 0.0171(5) 0.0200(5) 0.0221(6) -0.0017(5) -0.0009(5) 0.0010(5)
C9 0.0161(6) 0.0281(6) 0.0232(6) -0.0053(5) 0.0024(5) 0.0000(5)
C10 0.0190(6) 0.0286(6) 0.0182(5) -0.0001(5) 0.0019(5) -0.0089(5)
C11 0.0208(6) 0.0191(6) 0.0235(6) 0.0013(5) -0.0037(5) -0.0035(5)
C12 0.0149(5) 0.0196(5) 0.0229(6) -0.0027(5) -0.0002(5) 0.0003(4)
C13 0.0209(6) 0.0156(5) 0.0164(5) -0.0021(4) -0.0027(4) -0.0010(4)
C14 0.0223(6) 0.0192(6) 0.0209(6) -0.0034(5) -0.0004(5) 0.0013(5)
C15 0.0296(7) 0.0277(6) 0.0203(6) -0.0006(5) 0.0034(5) -0.0013(6)
C16 0.0367(8) 0.0229(6) 0.0211(6) 0.0027(5) -0.0028(6) -0.0021(6)
C17 0.0296(7) 0.0202(6) 0.0246(6) -0.0002(5) -0.0060(5) 0.0037(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.7399(13) . ?
S1 O5 1.4398(9) . ?
S1 O4 1.4410(9) . ?
S1 C13 1.7844(12) . ?
S1 C4 1.8189(12) . ?
N1 C13 1.3381(16) . ?
N1 C17 1.3383(17) . ?
O1 C1 1.2020(18) . ?
O2 C5 1.1993(16) . ?
O3 C5 1.3301(15) . ?
O3 C6 1.4560(17) . ?
C1 C2 1.4987(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.5419(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.5252(16) . ?
C3 C4 1.5398(16) . ?
C3 H3 1.0000 . ?
C4 C5 1.5312(16) . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3924(17) . ?
C7 C12 1.3953(17) . ?
C8 C9 1.3954(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3842(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3824(18) . ?
C11 C12 1.3931(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3806(18) . ?
C14 C15 1.3968(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O4 119.33(6) . . ?
O5 S1 C13 108.33(6) . . ?
O4 S1 C13 108.56(6) . . ?
O5 S1 C4 109.24(6) . . ?
O4 S1 C4 106.56(6) . . ?
C13 S1 C4 103.73(5) . . ?
C13 N1 C17 115.86(11) . . ?
C5 O3 C6 115.04(11) . . ?
O1 C1 C2 124.22(12) . . ?
O1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 114.09(11) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C7 C3 C4 111.88(10) . . ?
C7 C3 C2 111.91(10) . . ?
C4 C3 C2 107.76(10) . . ?
C7 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C5 C4 C3 111.57(10) . . ?
C5 C4 S1 104.47(8) . . ?
C3 C4 S1 113.46(8) . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
S1 C4 H4 109.1 . . ?
O2 C5 O3 125.49(12) . . ?
O2 C5 C4 123.39(11) . . ?
O3 C5 C4 111.12(10) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.15(11) . . ?
C8 C7 C3 120.23(11) . . ?
C12 C7 C3 120.61(11) . . ?
C7 C8 C9 120.80(12) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.61(12) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 121.96(12) . . ?
C11 C10 Cl1 118.39(10) . . ?
C9 C10 Cl1 119.65(10) . . ?
C10 C11 C12 118.80(12) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C7 120.68(11) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C13 C14 126.32(11) . . ?
N1 C13 S1 113.40(9) . . ?
C14 C13 S1 120.28(10) . . ?
C13 C14 C15 116.51(12) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
C16 C15 C14 118.86(13) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.49(12) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
N1 C17 C16 122.95(12) . . ?
N1 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.042